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Brian Halligan: evaluation

15 Feb 2026 Lenny's Podcast Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot)

“I think CEOs and everyone dramatically overrates their ability to interview, and overrates their gut feeling, and underrates a really high quality blind reference.”

— Brian Halligan

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Speaker
Brian Halligan
Attribution
Verified speaker
Claim type
evaluation
Recorded
15 Feb 2026
Publisher
Lenny's Podcast

Transcript context

…Okay, I have a bunch of questions along these lines, because one, you've been a CEO of an incredibly successful company for a long time, for about 20 years, before you moved on to this new chapter, now you work with a bunch of CEOs, you're Sequoia's in-house CEO coach, there's a few things that I've heard you do. One is you gather groups of CEOs, and what I've read is that you have kind of two tables. You have the kids table and the adults table. The kids table is CEOs that are companies that are about under 100 employees, the adult table is over 100 employees. So, let me ask you just, when you look at CEOs that move from the kids table to the adult table, other than just they scale and grow, what is it that these CEOs that graduate from kids to adults table do differently? The adults are really focused on, all they really want to talk about is their exec team. Their direct reports, how do you build our exec team, that next level down, org design... You would be surprised how much they think about that. And on average, I would say the adults are spending half their time just recruiting and interviewing. It's pretty all consuming. And I remember that from that phase in HubSpot's growth. And it surprises people like, wow, my job is really just to interview and hire, I didn't know that was going to be the case. So, that is one that they are making that transition, and I would just say in general, people are very bad at this, and HubSpot was too. I think CEOs and everyone dramatically overrates their ability to interview, and overrates their gut feeling, and underrates a really high quality blind reference. And I interviewed Dave, the CEO from MongoDB the other day, and he had an interesting [inaudible 00:07:22]. On average over his 10-year lifespan as a CEO of Mongo, there were two C-levels turned over per year. That's a lot of turnover at the top, and I didn't keep track of it like Dave, but I think HubSpot was kind of similar. And all of these startups are kind of similar too. And so, people are working on that, and struggling with it, is one thing in common with all of them. What do you do when you coach someone on that? When you're like, okay, you think you're amazing at interviewing, you think you know who's going to work out, what advice do you give them to help them develop that skill?…

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